dimethyl 2-(but-2-ynyl)-2-((1Z,3E)-4-cyclohexyl-2-(triisopropylsilyloxy)buta-1,3-dienyl)malonate

Base Information

• Chemical Name: dimethyl 2-(but-2-ynyl)-2-((1Z,3E)-4-cyclohexyl-2-(triisopropylsilyloxy)buta-1,3-dienyl)malonate
• CAS No.: 1357173-20-6
• Molecular Formula: C₂₈H₄₆O₅Si
• Molecular Weight: 490.756

Synonyms:dimethyl 2-(but-2-ynyl)-2-((1Z,3E)-4-cyclohexyl-2-(triisopropylsilyloxy)buta-1,3-dienyl)malonate

Chemical Property of dimethyl 2-(but-2-ynyl)-2-((1Z,3E)-4-cyclohexyl-2-(triisopropylsilyloxy)buta-1,3-dienyl)malonate

Chemical Property:

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Technology Process of dimethyl 2-(but-2-ynyl)-2-((1Z,3E)-4-cyclohexyl-2-(triisopropylsilyloxy)buta-1,3-dienyl)malonate

There total 3 articles about dimethyl 2-(but-2-ynyl)-2-((1Z,3E)-4-cyclohexyl-2-(triisopropylsilyloxy)buta-1,3-dienyl)malonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

(E)-dimethyl 2-(but-2-ynyl)-2-(4-cyclohexyl-2-oxobut-3-enyl)malonate (1357173-70-6) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → dimethyl 2-(but-2-ynyl)-2-((1Z,3E)-4-cyclohexyl-2-(triisopropylsilyloxy)buta-1,3-dienyl)malonate (1357173-20-6)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/ja210388g

Reference yield:

(E)-1-bromo-4-cyclohexylbut-3-en-2-one (1005481-58-2) → dimethyl 2-(but-2-ynyl)-2-((1Z,3E)-4-cyclohexyl-2-(triisopropylsilyloxy)buta-1,3-dienyl)malonate (1357173-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 20 °C / Inert atmosphere

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; mineral oil;

DOI:10.1021/ja210388g

Reference yield:

dimethyl propargylmalonate (107428-17-1) → dimethyl 2-(but-2-ynyl)-2-((1Z,3E)-4-cyclohexyl-2-(triisopropylsilyloxy)buta-1,3-dienyl)malonate (1357173-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 20 °C / Inert atmosphere

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; mineral oil;

DOI:10.1021/ja210388g

upstream raw materials:

(E)-1-bromo-4-cyclohexylbut-3-en-2-one

(E)-dimethyl 2-(but-2-ynyl)-2-(4-cyclohexyl-2-oxobut-3-enyl)malonate

triisopropylsilyl trifluoromethanesulfonate

dimethyl propargylmalonate

Downstream raw materials:

(3aS,4S,6aR)-dimethyl 4-cyclohexyl-3a-methyl-6-(triisopropylsilyloxy)-3a,4-dihydropentalene-1,1(6aH)-dicarboxylate

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